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Title: Glycosylated porphyrin derivatives and their photodynamic activity in cancer cells
Authors: Vedachalam, Seenuvasan
Choi, Bo-Hwa
Pasunooti, Kalyan Kumar
Ching, Kun Mei
Lee, Kijoon
Yoon, Ho Sup
Liu, Xue-Wei
Keywords: DRNTU::Science::Biological sciences::Cytology
Issue Date: 2011
Source: Vedachalam, S., Choi, B. H., Pasunooti, K. K., Ching, K. M., Lee, K., Yoon, H. S. & Liu, X. W. (2011). Glycosylated prophyrin derivatives and their photodynamic activity in tumor cells. Med. Chem. Commun., 2, 371-377.
Series/Report no.: Med. Chem. Commun.
Abstract: The present study reports the design and synthesis of nine C2-symmetric 5,15-[bis(arayl)]-10α,20β- [bis(1,2:3,4-di-O-isopropylidene-α-D-galactopyranose-6-yl)]porphyrins (3–11) bearing electron donating or electron withdrawing substituents and a D2-symmetric 5α,10β,15α,20β-tetrakis(1,2:3,4-di- O-isopropylidene-α-D-galactopyranose-6-yl)porphyrin (12). In the system we design, the C6 of pyranose sugar is elegantly fused into the porphyrin core as meso carbon, which renders a new type of photodynanic inducers. The biological effects of these derivatives were assessed in HeLa and HCT116 human cancer cells. In particular, the tetra-glycofused structure 12 exhibited the highest cellular uptake and photocytotoxicity. Unlike the reported sugar-porphyrin conjugates, which normally localize in mitochondria or endoplasmic reticulum, the unique glycofused porphyrins in this study were dominantly localized in lysosomes. The measurement of the dual flurorescence of annexin V-FITC/PI by flow cytometry revealed that the cell death was caused by apoptosis. Further PARP cleavage study suggested that apoptosis induced by the treatment of compound 12 was via caspase-dependent apoptotic pathway in cancer cells.
DOI: 10.1039/c0md00175a
Rights: © 2011 The Royal Society of Chemistry.  This is the author created version of a work that has been peer reviewed and accepted for publication by Med. Chem. Commun., The Royal Society of Chemistry.  It incorporates referee’s comments but changes resulting from the publishing process, such as copyediting, structural formatting, may not be reflected in this document.  The published version is available at: [DOI: ]
Fulltext Permission: open
Fulltext Availability: With Fulltext
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